#------------------------------------------------------------------------------ #$Date: 2024-09-06 02:46:32 +0300 (Fri, 06 Sep 2024) $ #$Revision: 294470 $ #$URL: file:///home/coder/svn-repositories/cod/cif/1/57/21/1572171.cif $ #------------------------------------------------------------------------------ # # This file is available in the Crystallography Open Database (COD), # http://www.crystallography.net/ # # All data on this site have been placed in the public domain by the # contributors. # data_1572171 loop_ _publ_author_name 'Sire, Charline' 'Meneyrol, Vincent' 'Saffon-Merceron, Nathalie' 'Terreno, Enzo' 'Garello, Francesca' 'Tei, Lorenzo' 'Jestin, Emmanuelle' 'Tripier, Raphaël' 'Troadec, Thibault' _publ_section_title ; A versatile fluorinated azamacrocyclic chelator enabling 18F PET or 19F MRI: a first step towards new multimodal and smart contrast agents. ; _journal_issue 33 _journal_name_full 'Chemical science' _journal_page_first 13550 _journal_page_last 13557 _journal_paper_doi 10.1039/d4sc02871f _journal_volume 15 _journal_year 2024 _chemical_formula_sum 'C22 H36 B2 F6 I6 N6' _chemical_formula_weight 1281.59 _space_group_crystal_system triclinic _space_group_IT_number 2 _space_group_name_Hall '-P 1' _space_group_name_H-M_alt 'P -1' _atom_sites_solution_hydrogens mixed _atom_sites_solution_primary 'dual space' _atom_sites_solution_secondary difmap _audit_creation_method SHELXL-2018/3 _audit_update_record ; 2023-12-13 deposited with the CCDC. 2024-07-17 downloaded from the CCDC. ; _cell_angle_alpha 75.784(3) _cell_angle_beta 67.305(3) _cell_angle_gamma 60.961(3) _cell_formula_units_Z 2 _cell_length_a 12.8808(5) _cell_length_b 12.9692(5) _cell_length_c 13.6306(5) _cell_measurement_reflns_used 6292 _cell_measurement_temperature 193(2) _cell_measurement_theta_max 66.53 _cell_measurement_theta_min 3.52 _cell_volume 1831.85(14) _computing_cell_refinement 'Bruker SAINT' _computing_data_collection 'Bruker APEX3' _computing_data_reduction 'Bruker SAINT' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _computing_structure_refinement 'SHELXL-2018/3 (Sheldrick, 2018)' _computing_structure_solution 'SHELXT (Sheldrick 2015)' _diffrn_ambient_temperature 193(2) _diffrn_detector_area_resol_mean 768x1024 _diffrn_measured_fraction_theta_full 0.996 _diffrn_measured_fraction_theta_max 0.996 _diffrn_measurement_device_type 'Bruker D8-Venture Photon III detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_radiation_type CuK\a _diffrn_radiation_wavelength 1.54178 _diffrn_reflns_av_unetI/netI 0.1010 _diffrn_reflns_Laue_measured_fraction_full 0.996 _diffrn_reflns_Laue_measured_fraction_max 0.996 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_number 6486 _diffrn_reflns_point_group_measured_fraction_full 0.996 _diffrn_reflns_point_group_measured_fraction_max 0.996 _diffrn_reflns_theta_full 66.770 _diffrn_reflns_theta_max 66.770 _diffrn_reflns_theta_min 3.524 _diffrn_source 'incoatec microfocus sealed tube' _exptl_absorpt_coefficient_mu 40.430 _exptl_absorpt_correction_T_max 0.7528 _exptl_absorpt_correction_T_min 0.3939 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS (Bruker-AXS)' _exptl_crystal_colour orange _exptl_crystal_density_diffrn 2.323 _exptl_crystal_description plate _exptl_crystal_F_000 1184 _exptl_crystal_size_max 0.060 _exptl_crystal_size_mid 0.050 _exptl_crystal_size_min 0.020 _refine_diff_density_max 1.491 _refine_diff_density_min -1.315 _refine_diff_density_rms 0.212 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.002 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 392 _refine_ls_number_reflns 6486 _refine_ls_number_restraints 1 _refine_ls_restrained_S_all 1.002 _refine_ls_R_factor_all 0.0984 _refine_ls_R_factor_gt 0.0541 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0524P)^2^] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1187 _refine_ls_wR_factor_ref 0.1381 _reflns_Friedel_coverage 0.000 _reflns_number_gt 4270 _reflns_number_total 6486 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d4sc02871f2.cif _cod_data_source_block H4Do2py2BF3+ _cod_depositor_comments 'Adding full bibliography for 1572170--1572172.cif.' _cod_original_cell_volume 1831.86(13) _cod_database_code 1572171 _shelx_shelxl_version_number 2018/3 _shelx_space_group_comment ; The symmetry employed for this shelxl refinement is uniquely defined by the following loop, which should always be used as a source of symmetry information in preference to the above space-group names. They are only intended as comments. ; _shelx_estimated_absorpt_t_min 0.195 _shelx_estimated_absorpt_t_max 0.499 _exptl_absorpt_special_details ; SADABS-2016/2 Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D., J. Appl. Cryst. 48 (2015) 3-10 ; _shelx_res_file ; TITL Do2py2BF3rouges_a.res in P-1 do2py2bf3rouges_a_tw.res created by SHELXL-2018/3 at 16:41:20 on 09-Oct-2020 CELL 1.54178 12.88080 12.96920 13.63060 75.7844 67.3054 60.9614 ZERR 2.00 0.00050 0.00050 0.00050 0.0027 0.0028 0.0025 LATT 1 SFAC C H B F N I UNIT 44 72 4 12 12 12 L.S. 10 ACTA HTAB N2 N1 HTAB N4 F4 HTAB N4 N3 HTAB N5 F4 HTAB N6 F3 EQIV $1 -x+1, -y+1, -z+1 HTAB C2 I3_$1 EQIV $2 x+1, y, z HTAB C3 I1_$2 HTAB C3 F1 HTAB C4 I6 HTAB C6 I6 EQIV $3 -x, -y+1, -z+1 HTAB C6 I2_$3 HTAB C7 F6 HTAB C8 I6 HTAB C9 F6 EQIV $4 -x, -y+2, -z+1 HTAB C9 I1_$4 EQIV $5 -x+1, -y+2, -z+1 HTAB C11 I6_$5 EQIV $6 x, y, z+1 HTAB C13 I6_$6 HTAB C14 I5_$6 HTAB C16 F1 HTAB C16 I6_$1 HTAB C18 I1_$3 HTAB C20 I2_$6 HTAB C21 I4_$6 HTAB C22 I3_$3 BOND $H FMAP 2 PLAN 20 SIZE 0.02 0.05 0.06 DFIX 0.85 0.01 N6 H6 TEMP -80.150 WGHT 0.052400 BASF 0.13073 FVAR 3.33636 I1 6 -0.181045 0.623977 0.346564 11.00000 0.04193 0.03295 = 0.05341 -0.00118 -0.01873 -0.01533 I2 6 0.017650 0.360225 0.353424 11.00000 0.05224 0.05479 = 0.03800 0.00675 -0.01833 -0.03574 I3 6 0.189003 0.118957 0.358036 11.00000 0.06700 0.04598 = 0.05051 0.00775 -0.03234 -0.03271 I4 6 0.048864 0.697665 0.324288 11.00000 0.05492 0.04263 = 0.04194 -0.00982 -0.02215 -0.00776 I5 6 0.224130 0.760090 0.332691 11.00000 0.05454 0.03758 = 0.03508 -0.00146 -0.01395 -0.01395 I6 6 0.444113 0.822592 0.344548 11.00000 0.03811 0.03421 = 0.03302 -0.00516 -0.00845 -0.01735 B1 3 0.539954 0.647378 0.895768 11.00000 0.04198 0.03704 = 0.03718 0.00407 -0.01975 -0.01806 F1 4 0.594675 0.523417 0.894610 11.00000 0.05101 0.04536 = 0.03542 0.00493 -0.01592 -0.01646 F2 4 0.551908 0.678323 0.979876 11.00000 0.05033 0.04799 = 0.04491 0.00066 -0.02284 -0.01972 F3 4 0.408800 0.687357 0.911715 11.00000 0.03950 0.04710 = 0.03502 0.00174 -0.01129 -0.02332 B2 3 0.035449 0.861293 0.906121 11.00000 0.03771 0.07587 = 0.03137 -0.00398 -0.00668 -0.03295 F4 4 0.155563 0.816779 0.920879 11.00000 0.03028 0.05068 = 0.03399 -0.01030 -0.01096 -0.01215 F5 4 -0.034343 0.813885 0.989702 11.00000 0.04155 0.08304 = 0.04015 -0.01830 0.00269 -0.02811 F6 4 -0.019120 0.983957 0.906960 11.00000 0.04697 0.04377 = 0.04515 -0.01304 -0.01405 -0.00600 N1 5 0.319311 0.948348 0.711178 11.00000 0.03237 0.02219 = 0.02668 -0.00608 -0.00607 -0.01137 N2 5 0.539238 0.718026 0.701561 11.00000 0.03249 0.03250 = 0.02483 0.00255 -0.00769 -0.02209 H2 2 0.441987 0.747835 0.741240 11.00000 -1.50000 N3 5 0.393747 0.597677 0.704633 11.00000 0.02977 0.01682 = 0.02964 -0.00589 -0.00950 -0.00786 N4 5 0.173128 0.826948 0.710279 11.00000 0.04018 0.03552 = 0.02026 -0.00335 -0.00807 -0.01603 H4 2 0.228772 0.800456 0.745537 11.00000 -1.50000 N5 5 0.273794 0.933065 0.948192 11.00000 0.03216 0.02934 = 0.04699 -0.01027 -0.01469 -0.00836 H5 2 0.227751 0.895515 0.954100 11.00000 -1.50000 N6 5 0.272458 0.564038 0.944446 11.00000 0.04436 0.03851 = 0.03680 -0.00223 -0.01603 -0.01809 H6 2 0.309810 0.605725 0.937542 11.00000 -1.50000 C1 1 0.447389 0.936718 0.661472 11.00000 0.03959 0.02588 = 0.02964 0.00178 -0.00934 -0.01392 AFIX 23 H1A 2 0.474393 0.948082 0.715270 11.00000 -1.20000 H1B 2 0.448160 0.999990 0.603573 11.00000 -1.20000 AFIX 0 C2 1 0.539234 0.818921 0.616354 11.00000 0.04796 0.04398 = 0.02180 0.00738 -0.00867 -0.03037 AFIX 23 H2A 2 0.624152 0.815282 0.586311 11.00000 -1.20000 H2B 2 0.517243 0.810115 0.557832 11.00000 -1.20000 AFIX 0 C3 1 0.599866 0.601465 0.653278 11.00000 0.01833 0.03448 = 0.03177 -0.00712 -0.00251 -0.00346 AFIX 23 H3A 2 0.674713 0.596349 0.591633 11.00000 -1.20000 H3B 2 0.627281 0.535877 0.706644 11.00000 -1.20000 AFIX 0 C4 1 0.510365 0.589216 0.617447 11.00000 0.03795 0.03906 = 0.01695 -0.01034 -0.00140 -0.01281 AFIX 23 H4A 2 0.488157 0.651803 0.560478 11.00000 -1.20000 H4B 2 0.552494 0.511878 0.586589 11.00000 -1.20000 AFIX 0 C5 1 0.296493 0.619271 0.659611 11.00000 0.03877 0.02684 = 0.02620 -0.00279 -0.00380 -0.01628 AFIX 23 H5A 2 0.233286 0.595419 0.714601 11.00000 -1.20000 H5B 2 0.335498 0.569459 0.598951 11.00000 -1.20000 AFIX 0 C6 1 0.231444 0.748554 0.621454 11.00000 0.03293 0.02210 = 0.02384 -0.00706 -0.00465 -0.00860 AFIX 23 H6A 2 0.293109 0.771255 0.562633 11.00000 -1.20000 H6B 2 0.166154 0.758797 0.593715 11.00000 -1.20000 AFIX 0 C7 1 0.145589 0.952914 0.667396 11.00000 0.04619 0.03336 = 0.02633 -0.00488 -0.01518 -0.00957 AFIX 23 H7A 2 0.110647 0.971915 0.608566 11.00000 -1.20000 H7B 2 0.081371 1.006210 0.724494 11.00000 -1.20000 AFIX 0 C8 1 0.259364 0.975597 0.627083 11.00000 0.04488 0.03369 = 0.01890 0.00117 -0.01748 -0.01205 AFIX 23 H8A 2 0.235351 1.059626 0.600467 11.00000 -1.20000 H8B 2 0.321140 0.926596 0.566427 11.00000 -1.20000 AFIX 0 C9 1 0.242999 1.045413 0.783571 11.00000 0.04682 0.02771 = 0.03686 -0.00876 -0.00915 -0.00850 AFIX 23 H9A 2 0.154618 1.058990 0.807692 11.00000 -1.20000 H9B 2 0.247465 1.118709 0.743372 11.00000 -1.20000 AFIX 0 C10 1 0.283045 1.022188 0.879075 11.00000 0.02424 0.02488 = 0.02539 -0.01090 0.00195 -0.00124 C11 1 0.325769 1.092494 0.901901 11.00000 0.04197 0.04308 = 0.04614 -0.00496 -0.00516 -0.02729 AFIX 43 H11 2 0.339061 1.154264 0.852612 11.00000 -1.20000 AFIX 0 C12 1 0.347635 1.068244 0.998723 11.00000 0.03378 0.06274 = 0.06653 -0.02008 -0.01687 -0.02111 AFIX 43 H12 2 0.374150 1.115770 1.016894 11.00000 -1.20000 AFIX 0 C13 1 0.331844 0.976938 1.069168 11.00000 0.05348 0.05353 = 0.03679 -0.00998 -0.02324 -0.01434 AFIX 43 H13 2 0.346138 0.961938 1.135736 11.00000 -1.20000 AFIX 0 C14 1 0.295562 0.908797 1.041962 11.00000 0.03593 0.04690 = 0.02601 0.00012 -0.00891 -0.00096 AFIX 43 H14 2 0.285572 0.844318 1.088818 11.00000 -1.20000 AFIX 0 C15 1 0.594993 0.710748 0.783799 11.00000 0.03755 0.04159 = 0.05149 0.01089 -0.02927 -0.01944 AFIX 23 H15A 2 0.575771 0.791406 0.795392 11.00000 -1.20000 H15B 2 0.687073 0.665369 0.757053 11.00000 -1.20000 AFIX 0 C16 1 0.422714 0.485079 0.773941 11.00000 0.05169 0.02318 = 0.04363 -0.00018 -0.00897 -0.00840 AFIX 23 H16A 2 0.492335 0.469350 0.798599 11.00000 -1.20000 H16B 2 0.450611 0.419075 0.731537 11.00000 -1.20000 AFIX 0 C17 1 0.311139 0.489170 0.869756 11.00000 0.04301 0.02950 = 0.03548 0.00221 -0.01390 -0.02261 C18 1 0.255858 0.417097 0.888396 11.00000 0.05577 0.02658 = 0.04592 0.00826 -0.02682 -0.02087 AFIX 43 H18 2 0.282512 0.364723 0.836466 11.00000 -1.20000 AFIX 0 C19 1 0.160846 0.419094 0.982472 11.00000 0.04963 0.03645 = 0.06539 0.00606 -0.02442 -0.02039 AFIX 43 H19 2 0.121320 0.369281 0.995253 11.00000 -1.20000 AFIX 0 C20 1 0.123351 0.497695 1.060091 11.00000 0.03176 0.03907 = 0.04249 0.00866 -0.00687 -0.00911 AFIX 43 H20 2 0.059722 0.500408 1.126191 11.00000 -1.20000 AFIX 0 C21 1 0.182597 0.569121 1.035683 11.00000 0.02539 0.04470 = 0.03900 0.00388 -0.01170 -0.01296 AFIX 43 H21 2 0.158511 0.623072 1.085275 11.00000 -1.20000 AFIX 0 C22 1 0.060104 0.817237 0.796420 11.00000 0.03795 0.05381 = 0.03059 0.00064 -0.00868 -0.02835 AFIX 23 H22A 2 0.073487 0.733869 0.807816 11.00000 -1.20000 H22B 2 -0.014594 0.865256 0.772530 11.00000 -1.20000 AFIX 0 HKLF 5 REM Do2py2BF3rouges_a.res in P-1 REM wR2 = 0.138074, GooF = S = 1.00240, Restrained GooF = 1.00232 for all data REM R1 = 0.054121 for 4270 Fo > 4sig(Fo) and 0.098390 for all 6486 data REM 392 parameters refined using 1 restraints END WGHT 0.0524 0.0000 REM Highest difference peak 1.491, deepest hole -1.315, 1-sigma level 0.212 Q1 1 0.2575 0.0607 0.3545 11.00000 0.05 1.49 Q2 1 0.5509 0.7821 0.3355 11.00000 0.05 1.21 Q3 1 0.1777 -0.0259 0.3469 11.00000 0.05 1.21 Q4 1 0.0426 0.3666 0.2715 11.00000 0.05 1.19 Q5 1 -0.2848 0.6642 0.3422 11.00000 0.05 1.18 Q6 1 0.0748 0.4635 0.3476 11.00000 0.05 1.09 Q7 1 0.0657 0.2923 0.3562 11.00000 0.05 1.08 Q8 1 0.2025 0.7593 0.4189 11.00000 0.05 1.08 Q9 1 0.0569 0.7355 0.6492 11.00000 0.05 1.05 Q10 1 0.1558 0.1122 0.4346 11.00000 0.05 1.03 Q11 1 -0.1351 0.6224 0.2661 11.00000 0.05 1.01 Q12 1 0.2257 1.1467 0.6649 11.00000 0.05 0.97 Q13 1 0.2331 0.5025 0.6416 11.00000 0.05 0.95 Q14 1 0.1213 0.7625 0.1938 11.00000 0.05 0.95 Q15 1 0.4801 0.8259 0.2696 11.00000 0.05 0.94 Q16 1 0.0387 1.0797 0.6739 11.00000 0.05 0.94 Q17 1 0.5315 0.3999 0.6703 11.00000 0.05 0.92 Q18 1 -0.2031 0.6119 0.4277 11.00000 0.05 0.92 Q19 1 0.2340 0.1222 0.2658 11.00000 0.05 0.91 Q20 1 0.2834 0.1822 0.3406 11.00000 0.05 0.89 ; _shelx_res_checksum 13527 _shelx_hkl_file ; 1 0 0 107430 3759 1 2 0 0 891 296 1 3 0 0 80334 3583 1 -4 0 -3 324748 11584 -2 4 0 0 324748 11584 1 5 0 0 501624 21274 1 6 0 0 21469 2714 1 7 0 0 12275 2640 1 8 0 0 156960 8203 1 9 0 0 -139 3330 1 10 0 0 5569 2297 1 11 0 0 7776 2609 1 12 0 0 2183 3673 1 -12 1 0 5983 3352 1 11 -1 8 12793 2745 -2 -11 1 0 12793 2745 1 -10 1 0 42058 4322 1 -9 1 0 924 2996 1 -8 1 0 4864 1874 1 7 -1 5 13567 2203 -2 -7 1 0 13567 2203 1 -6 1 0 -1452 1665 1 -5 1 0 323194 17776 1 -4 1 0 7440 909 1 3 -1 2 44612 1851 -2 -3 1 0 44612 1851 1 -2 1 0 28232 1225 1 -1 1 0 152828 5059 1 0 1 0 6867 358 1 1 1 0 2931 543 1 2 1 0 190238 9385 1 3 1 0 511 450 1 4 1 0 23789 1440 1 5 1 0 100159 4773 1 6 1 0 15444 2147 1 7 1 0 41621 3896 1 -8 -1 -6 51048 4855 -2 8 1 0 51048 4855 1 9 1 0 31256 3869 1 10 1 0 4691 2127 1 11 1 0 8197 2406 1 -12 -1 -9 29612 4818 -2 12 1 0 29612 4818 1 13 1 0 12630 7079 1 -11 2 0 5768 2533 1 10 -2 7 6327 2402 -2 -10 2 0 6327 2402 1 -9 2 0 15913 2762 1 -8 2 0 5246 2167 1 -7 2 0 14294 5870 1 -6 2 0 122103 6233 1 -5 2 0 98305 6095 1 -4 2 0 3491 934 1 -3 2 0 2398 643 1 -2 2 0 48630 2277 1 -1 2 0 128444 4658 1 0 2 0 220270 8316 1 -1 -2 -1 -110 290 -2 1 2 0 -110 290 1 2 2 0 178817 11687 1 3 2 0 158281 8885 1 4 2 0 415275 19266 1 -5 -2 -4 38142 2371 -2 5 2 0 38142 2371 1 6 2 0 611 760 1 7 2 0 128322 9418 1 8 2 0 51856 3869 1 -9 -2 -7 7684 4184 -2 9 2 0 7684 4184 1 10 2 0 46048 4788 1 11 2 0 3243 2561 1 12 2 0 42990 6328 1 13 2 0 2563 3145 1 -11 3 0 5795 2700 1 -10 3 0 7094 2654 1 -9 3 0 27154 3635 1 -8 3 0 6210 3243 1 -7 3 0 14710 2796 1 6 -3 4 277539 9857 -2 -6 3 0 277539 9857 1 -5 3 0 37312 2864 1 -4 3 0 23407 2071 1 -3 3 0 82909 4496 1 2 -3 1 419201 13946 -2 -2 3 0 419201 13946 1 -1 3 0 1403206 52367 1 0 3 0 40287 1834 1 1 3 0 28767 1415 1 -2 -3 -2 94300 5286 -2 2 3 0 94300 5286 1 3 3 0 468681 24951 1 4 3 0 396524 21428 1 5 3 0 8248 1888 1 6 3 0 105435 5524 1 7 3 0 74290 5028 1 8 3 0 30312 3104 1 9 3 0 17590 2898 1 10 3 0 -147 3293 1 11 3 0 2402 2535 1 12 3 0 3151 2551 1 13 3 0 2008 3154 1 -10 4 0 1004 3064 1 9 -4 6 6608 2996 -2 -9 4 0 6608 2996 1 -8 4 0 1440 4147 1 -7 4 0 11386 2235 1 -6 4 0 228921 9657 1 5 -4 3 40155 2750 -2 -5 4 0 40155 2750 1 -4 4 0 95336 5266 1 -3 4 0 17960 1752 1 -2 4 0 43406 2848 1 1 -4 0 12857 1054 -2 -1 4 0 12857 1054 1 0 4 0 168424 7291 1 1 4 0 151886 7197 1 2 4 0 1206 500 1 3 4 0 69893 3598 1 4 4 0 238125 10406 1 5 4 0 179565 10374 1 6 4 0 124554 5877 1 7 4 0 68788 3651 1 8 4 0 142596 8116 1 9 4 0 21955 4855 1 -10 -4 -8 37804 7183 -2 10 4 0 37804 7183 1 11 4 0 54891 5790 1 12 4 0 23280 4246 1 13 4 0 9060 4298 1 -9 5 0 4714 3024 1 -8 5 0 -226 4013 1 -7 5 0 1134 1993 1 -6 5 0 28786 3255 1 -5 5 0 11643 1814 1 -4 5 0 34086 2575 1 -3 5 0 16899 3110 1 -2 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12 17552 3549 1 -4 1 12 6443 1926 1 -3 1 12 31341 4599 1 -2 1 12 1131 1942 1 -1 1 12 65841 5485 1 0 1 12 6112 2249 1 1 1 12 62609 4340 1 2 1 12 9236 2464 1 3 1 12 5869 2036 1 4 1 12 4752 1884 1 5 1 12 21250 3607 1 6 1 12 1190 2213 1 7 1 12 5498 2431 1 8 1 12 -2627 4507 1 9 1 12 68959 5698 1 10 1 12 22819 4187 1 11 1 12 2711 2727 1 -12 -1 3 6317 2491 -2 12 1 12 6317 2491 1 -4 2 12 12812 2224 1 -3 2 12 7458 2570 1 -2 2 12 68749 4879 1 -1 2 12 4130 2003 1 0 2 12 22804 2571 1 1 2 12 3666 1882 1 2 2 12 101488 5630 1 3 2 12 59417 4284 1 4 2 12 102638 5573 1 -5 -2 8 39016 3106 -2 5 2 12 39016 3106 1 6 2 12 16644 2509 1 7 2 12 98812 5898 1 8 2 12 5032 2862 1 9 2 12 20317 3835 1 10 2 12 1445 2597 1 11 2 12 -2490 2490 1 12 2 12 20951 4695 1 -4 3 12 1280 1561 1 -3 3 12 4049 2031 1 2 -3 13 922 1651 -2 -2 3 12 922 1651 1 -1 3 12 18054 2338 1 0 3 12 1434 1733 1 1 3 12 12889 3981 1 2 3 12 1840 1909 1 3 3 12 12666 2261 1 4 3 12 34470 2783 1 5 3 12 18816 2504 1 6 3 12 1721 1943 1 7 3 12 -239 2021 1 8 3 12 4434 2679 1 9 3 12 165512 9751 1 10 3 12 44188 6916 1 11 3 12 32182 5347 1 12 3 12 6224 3826 1 13 3 12 12182 5037 1 -3 4 12 3787 1872 1 -2 4 12 32742 3142 1 -1 4 12 3013 1630 1 0 4 12 17655 2223 1 1 4 12 1691 1699 1 2 4 12 4474 1816 1 3 4 12 7138 2105 1 4 4 12 18157 2335 1 5 4 12 14320 2308 1 6 4 12 45865 3490 1 7 4 12 1806 2211 1 8 4 12 95507 6309 1 9 4 12 937 2480 1 -10 -4 4 18508 3246 -2 10 4 12 18508 3246 1 11 4 12 -793 2469 1 12 4 12 2772 3582 1 13 4 12 3540 3828 1 -3 5 12 18687 4807 1 -2 5 12 13314 2015 1 -1 5 12 4350 1613 1 0 5 12 4938 1678 1 1 5 12 27341 2794 1 2 5 12 11260 2512 1 -3 -5 9 96544 5064 -2 3 5 12 96544 5064 1 4 5 12 7450 2035 1 5 5 12 2275 1876 1 6 5 12 100431 5138 1 7 5 12 3068 2264 1 8 5 12 1331 2376 1 9 5 12 -1659 2269 1 10 5 12 -848 2260 1 11 5 12 37129 4255 1 12 5 12 3970 2580 1 13 5 12 6563 2731 1 -2 6 12 6293 1666 1 -1 6 12 -1514 1514 1 0 6 12 19276 2104 1 1 6 12 1598 1626 1 2 6 12 8947 2308 1 3 6 12 90612 7210 1 4 6 12 9979 2118 1 5 6 12 1203 1903 1 6 6 12 3233 2075 1 7 6 12 31534 3320 1 8 6 12 214000 10769 1 9 6 12 42168 3969 1 10 6 12 10034 2801 1 11 6 12 15552 2963 1 12 6 12 23476 3263 1 13 6 12 39081 4798 1 -1 7 12 1793 2088 1 0 7 12 900 1651 1 1 7 12 6832 1784 1 2 7 12 -471 1735 1 3 7 12 90826 5177 1 4 7 12 16188 2497 1 5 7 12 27161 3104 1 6 7 12 8168 2480 1 7 7 12 42463 6136 1 8 7 12 12844 2498 1 9 7 12 54938 5268 1 10 7 12 4227 2589 1 11 7 12 -1690 2111 1 -12 -7 2 2239 2935 -2 12 7 12 2239 2935 1 13 7 12 -1709 2994 1 0 8 12 445 1556 1 1 8 12 1928 1606 1 2 8 12 31883 3543 1 3 8 12 684 1971 1 4 8 12 -1832 2154 1 5 8 12 25161 3710 1 6 8 12 27321 5105 1 7 8 12 -137 2244 1 8 8 12 62 2305 1 9 8 12 14744 2872 1 10 8 12 3389 2459 1 11 8 12 846 2304 1 12 8 12 1338 2622 1 13 8 12 455 2616 1 1 9 12 4249 1948 1 2 9 12 41140 3353 1 3 9 12 -1973 1973 1 4 9 12 2047 2136 1 5 9 12 -357 2188 1 6 9 12 31712 3746 1 7 9 12 144608 8263 1 8 9 12 736 2252 1 9 9 12 2609 2475 1 10 9 12 18019 4191 1 11 9 12 30853 4143 1 12 9 12 21566 3192 1 13 9 12 1364 3995 1 2 10 12 43046 6871 1 3 10 12 14541 2445 1 4 10 12 7495 2735 1 5 10 12 5546 2126 1 6 10 12 29309 5202 1 7 10 12 16936 3290 1 8 10 12 44591 4592 1 9 10 12 2443 2243 1 -10 -10 3 -2373 2373 -2 10 10 12 -2373 2373 1 11 10 12 4552 2613 1 12 10 12 -2672 2672 1 13 10 12 16561 3793 1 3 11 12 6780 2140 1 4 11 12 -1759 1759 1 5 11 12 13429 2659 1 6 11 12 10608 2866 1 7 11 12 10618 2513 1 8 11 12 1465 2437 1 9 11 12 15563 15132 1 10 11 12 17647 3065 1 11 11 12 16874 3438 1 12 11 12 -949 2601 1 5 12 12 9414 2283 1 6 12 12 40956 3546 1 7 12 12 -2124 2555 1 8 12 12 2822 3016 1 9 12 12 5393 5752 1 10 12 12 18396 6385 1 11 12 12 673 3255 1 -1 -5 13 3445 1685 1 0 -5 13 10560 2073 1 1 -5 13 2140 1941 1 2 -5 13 12062 2079 1 3 -5 13 2213 2570 1 4 -5 13 -157 2775 1 -2 -4 13 1648 1920 1 -1 -4 13 17519 4225 1 0 -4 13 14568 2332 1 1 -4 13 28038 3016 1 2 -4 13 4237 2428 1 3 -4 13 9160 3459 1 4 -4 13 8473 2974 1 5 -4 13 3105 2181 1 6 -4 13 1983 3678 1 -3 -3 13 7013 2449 1 -2 -3 13 1803 1815 1 -1 -3 13 261 1886 1 0 -3 13 4309 2040 1 1 -3 13 54433 4580 1 -2 3 12 7366 2586 -2 2 -3 13 7366 2586 1 3 -3 13 3658 1998 1 4 -3 13 8956 2284 1 5 -3 13 6858 2372 1 6 -3 13 90152 5990 1 7 -3 13 36043 3432 1 -3 -2 13 241 3471 1 -2 -2 13 1039 2876 1 -1 -2 13 6571 2194 1 0 -2 13 6594 2220 1 1 -2 13 39926 4510 1 2 -2 13 41434 7029 1 3 -2 13 47741 4293 1 4 -2 13 4916 3193 1 5 -2 13 39797 3486 1 6 -2 13 4319 2538 1 7 -2 13 35114 5003 1 8 -2 13 3131 2734 1 -3 -1 13 77 1801 1 -2 -1 13 7500 2160 1 -1 -1 13 -876 1961 1 0 -1 13 46473 5775 1 1 -1 13 4185 2293 1 2 -1 13 8166 2376 1 3 -1 13 11602 2409 1 4 -1 13 42243 4892 1 5 -1 13 -796 2314 1 6 -1 13 2819 2169 1 -7 1 8 8609 2255 -2 7 -1 13 8609 2255 1 8 -1 13 -145 2118 1 9 -1 13 6822 4103 1 -3 0 13 1362 1717 1 -2 0 13 3089 1914 1 -1 0 13 -464 1989 1 0 0 13 74794 5262 -2 0 0 13 74794 5262 1 1 0 13 8852 2662 1 2 0 13 -1874 1874 1 3 0 13 8965 2865 1 4 0 13 38633 3829 1 5 0 13 138119 6980 1 6 0 13 16348 2773 1 7 0 13 5495 2254 1 8 0 13 25965 3242 1 9 0 13 20191 3474 1 10 0 13 6183 2419 1 -3 1 13 6510 1786 1 -2 1 13 15275 2371 1 -1 1 13 20020 2703 1 0 1 13 63170 4629 1 1 1 13 70099 4409 1 2 1 13 15831 2472 1 3 1 13 1252 1983 1 4 1 13 31558 3135 1 5 1 13 801 2071 1 6 1 13 78984 5362 1 7 1 13 1106 2119 1 8 1 13 13143 2659 1 9 1 13 12340 3047 1 10 1 13 8092 2875 1 11 1 13 937 2243 1 -3 2 13 -643 2864 1 -2 2 13 22006 2717 1 -1 2 13 14970 2484 1 0 2 13 4857 1914 1 1 2 13 12671 2124 1 2 2 13 449 2071 1 3 2 13 100909 5133 1 4 2 13 383 1757 1 -5 -2 9 3644 2654 -2 5 2 13 3644 2654 1 6 2 13 7477 4001 1 7 2 13 9540 2493 1 8 2 13 54816 4522 1 9 2 13 16132 7020 1 10 2 13 -1004 3218 1 11 2 13 4836 2624 1 2 -3 14 1106 1755 -2 -2 3 13 1106 1755 1 -1 3 13 39215 3536 1 0 3 13 2489 1789 1 1 3 13 4843 1773 1 2 3 13 -1320 1656 1 3 3 13 10381 1993 1 4 3 13 76261 4415 1 5 3 13 4650 1918 1 6 3 13 1471 2034 1 7 3 13 3941 2742 1 8 3 13 25900 3776 1 9 3 13 2103 4873 1 10 3 13 3249 2531 1 11 3 13 30539 3949 1 12 3 13 4210 2439 1 -2 4 13 21959 2658 1 -1 4 13 30041 4280 1 0 4 13 29137 2631 1 1 4 13 4108 1693 1 2 4 13 867 1756 1 3 4 13 71521 4645 1 4 4 13 1830 1832 1 5 4 13 44880 3341 1 6 4 13 2316 2062 1 7 4 13 1790 2342 1 8 4 13 25424 3570 1 9 4 13 6547 2593 1 -10 -4 5 4179 2397 -2 10 4 13 4179 2397 1 11 4 13 -1812 2311 1 12 4 13 -1756 5787 1 -1 5 13 6352 1726 1 0 5 13 6785 1682 1 1 5 13 22848 3260 1 2 5 13 70555 4231 1 -3 -5 10 24563 2527 -2 3 5 13 24563 2527 1 4 5 13 38867 3090 1 5 5 13 1049 1873 1 6 5 13 51744 4578 1 7 5 13 41019 7212 1 8 5 13 14704 2949 1 9 5 13 4170 2529 1 10 5 13 1449 3102 1 11 5 13 73509 5415 1 12 5 13 11567 6473 1 13 5 13 326 4288 1 -1 6 13 -1071 1598 1 0 6 13 8408 1689 1 1 6 13 -207 1544 1 2 6 13 9674 2678 1 3 6 13 9882 1909 1 4 6 13 -656 2788 1 5 6 13 124 2010 1 6 6 13 3210 2913 1 7 6 13 6973 2804 1 8 6 13 43539 4061 1 9 6 13 11576 2804 1 10 6 13 16053 2867 1 11 6 13 -942 2485 1 12 6 13 7697 2228 1 13 6 13 44173 4769 1 0 7 13 1879 1592 1 1 7 13 4601 1679 1 2 7 13 18173 2208 1 3 7 13 3446 1784 1 4 7 13 6260 2133 1 5 7 13 23849 3075 1 6 7 13 830 2408 1 7 7 13 16241 4224 1 8 7 13 9599 2892 1 9 7 13 11911 2540 1 10 7 13 -539 2382 1 11 7 13 -968 1968 1 -12 -7 3 30224 6214 -2 12 7 13 30224 6214 1 13 7 13 -4239 5045 1 1 8 13 13017 2023 1 2 8 13 39532 3895 1 3 8 13 5159 2834 1 4 8 13 3636 1900 1 5 8 13 27076 3364 1 6 8 13 7927 2500 1 7 8 13 37846 7242 1 8 8 13 2715 2213 1 9 8 13 2440 2119 1 10 8 13 77542 5244 1 11 8 13 1347 2248 1 12 8 13 2865 2343 1 13 8 13 2833 2478 1 2 9 13 26 1966 1 3 9 13 -535 1852 1 4 9 13 1395 5308 1 5 9 13 6973 2272 1 6 9 13 -408 2194 1 7 9 13 89225 7409 1 8 9 13 10585 2572 1 9 9 13 7355 2787 1 10 9 13 -1996 1996 1 11 9 13 19315 2784 1 12 9 13 51268 3893 1 3 10 13 4625 1794 1 4 10 13 6064 1850 1 5 10 13 8683 1991 1 6 10 13 25861 2873 1 7 10 13 14039 2774 1 8 10 13 25698 2906 1 9 10 13 9373 2591 1 -10 -10 4 4135 2379 -2 10 10 13 4135 2379 1 11 10 13 11363 3727 1 12 10 13 -656 2290 1 5 11 13 603 3811 1 6 11 13 5449 2794 1 7 11 13 3362 2124 1 8 11 13 6618 2813 1 9 11 13 18964 5084 1 10 11 13 6340 2914 1 11 11 13 1293 2898 1 1 -4 14 7500 1904 1 2 -4 14 2073 1723 1 3 -4 14 2158 3067 1 4 -4 14 23285 4288 1 -1 -3 14 1215 1548 1 0 -3 14 9431 2952 1 1 -3 14 -1609 1609 1 -2 3 13 6683 2560 -2 2 -3 14 6683 2560 1 3 -3 14 1154 3478 1 4 -3 14 -2703 4776 1 5 -3 14 5310 2133 1 6 -3 14 29289 3261 1 -1 -2 14 11757 2140 1 0 -2 14 7214 1926 1 1 -2 14 5563 2107 1 2 -2 14 6693 4622 1 3 -2 14 1391 1918 1 4 -2 14 2844 5944 1 5 -2 14 23439 3243 1 6 -2 14 8462 3299 1 7 -2 14 12102 2331 1 -1 -1 14 41651 3756 1 0 -1 14 43648 4105 1 1 -1 14 3760 2116 1 2 -1 14 2993 2116 1 3 -1 14 52075 5664 1 4 -1 14 630 2114 1 5 -1 14 28703 4238 1 6 -1 14 10585 2290 1 -7 1 9 -136 1850 -2 7 -1 14 -136 1850 1 8 -1 14 15358 2563 1 -2 0 14 1209 1522 1 -1 0 14 5241 1776 1 0 0 14 9774 2233 -2 0 0 14 9774 2233 1 1 0 14 4508 1931 1 2 0 14 1804 2137 1 3 0 14 157 2105 1 4 0 14 5720 1979 1 5 0 14 77434 5420 1 6 0 14 42819 3886 1 7 0 14 4487 2094 1 8 0 14 5084 2257 1 9 0 14 6780 2342 1 -1 1 14 2152 1787 1 0 1 14 21495 2806 1 1 1 14 6813 3308 1 2 1 14 29086 2841 1 3 1 14 1758 2237 1 4 1 14 33083 3035 1 5 1 14 30411 7232 1 6 1 14 62250 5240 1 7 1 14 17854 2780 1 8 1 14 10504 6942 1 9 1 14 14617 9037 1 10 1 14 -2985 3311 1 -1 2 14 22904 6353 1 0 2 14 -789 1671 1 1 2 14 -80 1760 1 2 2 14 6030 2213 1 3 2 14 18442 2346 1 4 2 14 19075 2343 1 -5 -2 10 2870 1831 -2 5 2 14 2870 1831 1 6 2 14 521 2570 1 7 2 14 8915 2490 1 8 2 14 9041 2640 1 9 2 14 -694 2837 1 10 2 14 -364 2322 1 -1 3 14 2213 1978 1 0 3 14 -368 2208 1 1 3 14 2903 1699 1 2 3 14 4154 1688 1 3 3 14 1012 1996 1 4 3 14 132044 6368 1 5 3 14 15391 2262 1 6 3 14 7043 2191 1 7 3 14 14859 2464 1 8 3 14 38883 4178 1 9 3 14 65374 5374 1 10 3 14 13364 3004 1 11 3 14 3951 2168 1 -1 4 14 23742 2539 1 0 4 14 8040 1911 1 1 4 14 15163 1978 1 2 4 14 6339 2706 1 3 4 14 64789 4012 1 4 4 14 27930 2600 1 5 4 14 96281 5241 1 6 4 14 946 2897 1 7 4 14 2821 2417 1 8 4 14 8659 2604 1 9 4 14 3964 3314 1 10 4 14 24271 4744 1 11 4 14 -1263 1918 1 0 5 14 6083 3218 1 1 5 14 277 1395 1 2 5 14 23382 2234 1 -3 -5 11 6705 1794 -2 3 5 14 6705 1794 1 4 5 14 6775 1797 1 5 5 14 1150 1884 1 6 5 14 -1889 1889 1 7 5 14 46632 4723 1 8 5 14 12673 2679 1 9 5 14 8970 2698 1 10 5 14 18333 4244 1 11 5 14 5310 2765 1 12 5 14 6513 3185 1 1 6 14 -1936 2015 1 2 6 14 950 1573 1 3 6 14 53895 3585 1 4 6 14 -1020 1609 1 5 6 14 4532 2031 1 6 6 14 4309 2247 1 7 6 14 47934 4142 1 8 6 14 15924 2908 1 9 6 14 2524 2164 1 10 6 14 10453 2331 1 11 6 14 13756 3542 1 12 6 14 3450 2368 1 2 7 14 37152 3050 1 3 7 14 28699 3255 1 4 7 14 54492 3987 1 5 7 14 2952 2781 1 6 7 14 45 3138 1 7 7 14 2893 2645 1 8 7 14 4097 2389 1 9 7 14 20962 2882 1 10 7 14 1912 2068 1 11 7 14 -659 2601 1 -12 -7 4 20541 8413 -2 12 7 14 20541 8413 1 2 8 14 1140 2714 1 3 8 14 8270 2104 1 4 8 14 -2338 3469 1 5 8 14 8131 2177 1 6 8 14 23166 6025 1 7 8 14 26020 5007 1 8 8 14 15389 2727 1 9 8 14 4385 3075 1 10 8 14 44031 3904 1 11 8 14 13228 2809 1 12 8 14 -33 2514 1 4 9 14 10961 2664 1 5 9 14 1987 2570 1 6 9 14 8791 2383 1 7 9 14 499 2020 1 8 9 14 -2161 2161 1 9 9 14 3476 2080 1 10 9 14 3124 2944 1 11 9 14 648 2077 1 5 10 14 3211 1678 1 6 10 14 -326 1645 1 7 10 14 620 1751 1 8 10 14 -1753 1753 1 9 10 14 7888 2792 1 -10 -10 5 2748 2393 -2 10 10 14 2748 2393 1 2 -2 15 33540 4144 1 3 -2 15 4680 2004 1 4 -2 15 8531 4143 1 1 -1 15 3093 1855 1 2 -1 15 14 2632 1 3 -1 15 12588 2234 1 4 -1 15 24953 3196 1 5 -1 15 4983 2548 1 6 -1 15 3230 2016 1 1 0 15 -220 1649 1 2 0 15 849 1780 1 3 0 15 -1451 2989 1 4 0 15 10405 2341 1 5 0 15 11454 2197 1 6 0 15 2611 1772 1 7 0 15 1011 2513 1 1 1 15 16030 4079 1 2 1 15 3050 2750 1 3 1 15 9485 2228 1 4 1 15 -1609 1733 1 5 1 15 5302 1946 1 6 1 15 -1752 2139 1 7 1 15 6965 2094 1 8 1 15 4667 2120 1 1 2 15 2718 1833 1 2 2 15 23425 2702 1 3 2 15 22602 2349 1 4 2 15 45183 3867 1 -5 -2 11 18991 2387 -2 5 2 15 18991 2387 1 6 2 15 7085 2005 1 7 2 15 29713 3739 1 8 2 15 1317 2121 1 9 2 15 4663 2123 1 1 3 15 1160 4099 1 2 3 15 3931 1858 1 3 3 15 1500 1749 1 4 3 15 19400 3410 1 5 3 15 3518 1832 1 6 3 15 -1684 1684 1 7 3 15 -1902 2413 1 8 3 15 8585 4697 1 9 3 15 81303 6092 1 10 3 15 19412 2914 1 1 4 15 41 2182 1 2 4 15 17761 1948 1 3 4 15 1616 1530 1 4 4 15 6118 1924 1 5 4 15 11048 2079 1 6 4 15 22050 2759 1 7 4 15 3005 1994 1 8 4 15 23851 2735 1 9 4 15 5669 2263 1 10 4 15 27926 3836 1 2 5 15 2781 2321 1 3 5 15 30244 2596 1 4 5 15 3054 1892 1 5 5 15 543 1908 1 6 5 15 12842 2609 1 7 5 15 2114 1972 1 8 5 15 831 2696 1 9 5 15 2116 2276 1 10 5 15 2201 2092 1 3 6 15 24363 2800 1 4 6 15 -135 2147 1 5 6 15 2064 1830 1 6 6 15 764 3278 1 7 6 15 40629 20182 1 8 6 15 73455 5130 1 9 6 15 10275 2883 1 10 6 15 -257 1759 1 4 7 15 14739 2164 1 5 7 15 6378 3297 1 6 7 15 1213 3823 1 7 7 15 22505 3178 1 8 7 15 14672 2679 1 9 7 15 47583 3929 1 10 7 15 3719 1849 1 5 8 15 5240 3010 1 6 8 15 19710 2731 1 7 8 15 -705 2226 1 8 8 15 -1413 1989 1 9 8 15 8787 2108 1 10 8 15 -638 1719 1 7 9 15 48290 6350 1 8 9 15 4616 2130 1 9 9 15 -1898 2403 1 4 2 16 -951 1924 1 -5 -2 12 6934 1975 -2 5 2 16 6934 1975 1 6 2 16 3093 2853 1 4 3 16 8412 3384 1 5 3 16 -23 2053 1 6 3 16 -1891 1891 1 7 3 16 -2043 2043 1 4 4 16 2104 2389 1 5 4 16 6055 2142 1 6 4 16 1825 1931 1 7 4 16 142 2218 1 8 4 16 9220 4475 1 5 5 16 906 1861 1 6 5 16 20640 2808 1 7 5 16 7209 2045 1 8 5 16 16739 3257 1 6 6 16 6553 3015 1 7 6 16 1195 1929 1 ; _shelx_hkl_checksum 79888 loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, -y, -z' loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_site_symmetry_order _atom_site_calc_flag _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group I1 I -0.18105(8) 0.62398(7) 0.34656(7) 0.0424(2) Uani 1 1 d . . . . . I2 I 0.01765(8) 0.36022(8) 0.35342(7) 0.0435(2) Uani 1 1 d . . . . . I3 I 0.18900(9) 0.11896(8) 0.35804(7) 0.0485(3) Uani 1 1 d . . . . . I4 I 0.04886(9) 0.69767(8) 0.32429(7) 0.0488(3) Uani 1 1 d . . . . . I5 I 0.22413(8) 0.76009(8) 0.33269(7) 0.0454(2) Uani 1 1 d . . . . . I6 I 0.44411(7) 0.82259(7) 0.34455(6) 0.0348(2) Uani 1 1 d . . . . . B1 B 0.5400(14) 0.6474(13) 0.8958(12) 0.037(4) Uani 1 1 d . . . . . F1 F 0.5947(7) 0.5234(6) 0.8946(5) 0.0468(19) Uani 1 1 d . . . . . F2 F 0.5519(7) 0.6783(6) 0.9799(6) 0.0467(19) Uani 1 1 d . . . . . F3 F 0.4088(6) 0.6874(6) 0.9117(5) 0.0397(17) Uani 1 1 d . . . . . B2 B 0.0354(15) 0.8613(17) 0.9061(12) 0.046(4) Uani 1 1 d . . . . . F4 F 0.1556(6) 0.8168(6) 0.9209(5) 0.0390(17) Uani 1 1 d . . . . . F5 F -0.0343(7) 0.8139(8) 0.9897(6) 0.057(2) Uani 1 1 d . . . . . F6 F -0.0191(7) 0.9840(7) 0.9070(6) 0.050(2) Uani 1 1 d . . . . . N1 N 0.3193(9) 0.9483(8) 0.7112(7) 0.028(2) Uani 1 1 d . . . . . N2 N 0.5392(9) 0.7180(8) 0.7016(7) 0.028(2) Uani 1 1 d . . . . . H2 H 0.442(11) 0.748(10) 0.741(10) 0.042 Uiso 1 1 d . U . . . N3 N 0.3937(8) 0.5977(8) 0.7046(7) 0.026(2) Uani 1 1 d . . . . . N4 N 0.1731(10) 0.8269(9) 0.7103(7) 0.032(2) Uani 1 1 d . . . . . H4 H 0.229(12) 0.800(11) 0.746(11) 0.049 Uiso 1 1 d . U . . . N5 N 0.2738(10) 0.9331(9) 0.9482(9) 0.036(3) Uani 1 1 d . . . . . H5 H 0.228(13) 0.896(12) 0.954(11) 0.054 Uiso 1 1 d . U . . . N6 N 0.2725(10) 0.5640(9) 0.9444(9) 0.039(3) Uani 1 1 d D . . . . H6 H 0.310(11) 0.606(10) 0.938(11) 0.058 Uiso 1 1 d D U . . . C1 C 0.4474(11) 0.9367(10) 0.6615(9) 0.033(3) Uani 1 1 d . . . . . H1A H 0.474393 0.948082 0.715270 0.040 Uiso 1 1 calc R U . . . H1B H 0.448160 0.999990 0.603573 0.040 Uiso 1 1 calc R U . . . C2 C 0.5392(12) 0.8189(11) 0.6164(9) 0.036(3) Uani 1 1 d . . . . . H2A H 0.624152 0.815282 0.586311 0.043 Uiso 1 1 calc R U . . . H2B H 0.517243 0.810115 0.557832 0.043 Uiso 1 1 calc R U . . . C3 C 0.5999(10) 0.6015(10) 0.6533(9) 0.033(3) Uani 1 1 d . . . . . H3A H 0.674713 0.596349 0.591633 0.039 Uiso 1 1 calc R U . . . H3B H 0.627281 0.535877 0.706644 0.039 Uiso 1 1 calc R U . . . C4 C 0.5104(11) 0.5892(11) 0.6174(8) 0.034(3) Uani 1 1 d . . . . . H4A H 0.488157 0.651803 0.560478 0.041 Uiso 1 1 calc R U . . . H4B H 0.552494 0.511878 0.586589 0.041 Uiso 1 1 calc R U . . . C5 C 0.2965(11) 0.6193(10) 0.6596(9) 0.032(3) Uani 1 1 d . . . . . H5A H 0.233286 0.595419 0.714601 0.038 Uiso 1 1 calc R U . . . H5B H 0.335498 0.569459 0.598951 0.038 Uiso 1 1 calc R U . . . C6 C 0.2314(11) 0.7486(9) 0.6215(9) 0.028(3) Uani 1 1 d . . . . . H6A H 0.293109 0.771255 0.562633 0.034 Uiso 1 1 calc R U . . . H6B H 0.166154 0.758797 0.593715 0.034 Uiso 1 1 calc R U . . . C7 C 0.1456(12) 0.9529(11) 0.6674(9) 0.037(3) Uani 1 1 d . . . . . H7A H 0.110647 0.971915 0.608566 0.044 Uiso 1 1 calc R U . . . H7B H 0.081371 1.006210 0.724494 0.044 Uiso 1 1 calc R U . . . C8 C 0.2594(11) 0.9756(11) 0.6271(8) 0.033(3) Uani 1 1 d . . . . . H8A H 0.235351 1.059626 0.600467 0.039 Uiso 1 1 calc R U . . . H8B H 0.321140 0.926596 0.566427 0.039 Uiso 1 1 calc R U . . . C9 C 0.2430(12) 1.0454(11) 0.7836(10) 0.041(3) Uani 1 1 d . . . . . H9A H 0.154618 1.058990 0.807692 0.049 Uiso 1 1 calc R U . . . H9B H 0.247465 1.118709 0.743372 0.049 Uiso 1 1 calc R U . . . C10 C 0.2830(10) 1.0222(10) 0.8791(9) 0.031(3) Uani 1 1 d . . . . . C11 C 0.3258(12) 1.0925(12) 0.9019(11) 0.042(3) Uani 1 1 d . . . . . H11 H 0.339061 1.154264 0.852612 0.051 Uiso 1 1 calc R U . . . C12 C 0.3476(12) 1.0682(14) 0.9987(12) 0.051(4) Uani 1 1 d . . . . . H12 H 0.374150 1.115770 1.016894 0.061 Uiso 1 1 calc R U . . . C13 C 0.3318(13) 0.9769(13) 1.0692(11) 0.048(4) Uani 1 1 d . . . . . H13 H 0.346138 0.961938 1.135736 0.057 Uiso 1 1 calc R U . . . C14 C 0.2956(12) 0.9088(12) 1.0420(10) 0.045(4) Uani 1 1 d . . . . . H14 H 0.285572 0.844318 1.088818 0.054 Uiso 1 1 calc R U . . . C15 C 0.5950(12) 0.7107(11) 0.7838(10) 0.040(3) Uani 1 1 d . . . . . H15A H 0.575771 0.791406 0.795392 0.048 Uiso 1 1 calc R U . . . H15B H 0.687073 0.665369 0.757053 0.048 Uiso 1 1 calc R U . . . C16 C 0.4227(13) 0.4851(11) 0.7739(10) 0.046(3) Uani 1 1 d . . . . . H16A H 0.492335 0.469350 0.798599 0.055 Uiso 1 1 calc R U . . . H16B H 0.450611 0.419075 0.731537 0.055 Uiso 1 1 calc R U . . . C17 C 0.3111(12) 0.4892(10) 0.8698(10) 0.033(3) Uani 1 1 d . . . . . C18 C 0.2559(12) 0.4171(11) 0.8884(11) 0.040(3) Uani 1 1 d . . . . . H18 H 0.282512 0.364723 0.836466 0.048 Uiso 1 1 calc R U . . . C19 C 0.1608(13) 0.4191(12) 0.9825(12) 0.050(4) Uani 1 1 d . . . . . H19 H 0.121320 0.369281 0.995253 0.060 Uiso 1 1 calc R U . . . C20 C 0.1234(12) 0.4977(11) 1.0601(11) 0.045(3) Uani 1 1 d . . . . . H20 H 0.059722 0.500408 1.126191 0.054 Uiso 1 1 calc R U . . . C21 C 0.1826(11) 0.5691(12) 1.0357(10) 0.038(3) Uani 1 1 d . . . . . H21 H 0.158511 0.623072 1.085275 0.046 Uiso 1 1 calc R U . . . C22 C 0.0601(12) 0.8172(12) 0.7964(9) 0.039(3) Uani 1 1 d . . . . . H22A H 0.073487 0.733869 0.807816 0.046 Uiso 1 1 calc R U . . . H22B H -0.014594 0.865256 0.772530 0.046 Uiso 1 1 calc R U . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 I1 0.0419(5) 0.0329(5) 0.0534(5) -0.0012(4) -0.0187(4) -0.0153(4) I2 0.0522(5) 0.0548(6) 0.0380(4) 0.0068(4) -0.0183(4) -0.0357(4) I3 0.0670(6) 0.0460(5) 0.0505(5) 0.0078(4) -0.0323(5) -0.0327(5) I4 0.0549(6) 0.0426(5) 0.0419(5) -0.0098(4) -0.0221(4) -0.0078(4) I5 0.0545(6) 0.0376(5) 0.0351(4) -0.0015(4) -0.0139(4) -0.0140(4) I6 0.0381(5) 0.0342(4) 0.0330(4) -0.0052(3) -0.0085(3) -0.0174(4) B1 0.042(9) 0.037(9) 0.037(8) 0.004(6) -0.020(7) -0.018(7) F1 0.051(5) 0.045(5) 0.035(4) 0.005(3) -0.016(4) -0.016(4) F2 0.050(5) 0.048(5) 0.045(4) 0.001(4) -0.023(4) -0.020(4) F3 0.039(4) 0.047(4) 0.035(4) 0.002(3) -0.011(3) -0.023(3) B2 0.038(9) 0.076(13) 0.031(8) -0.004(8) -0.007(7) -0.033(9) F4 0.030(4) 0.051(4) 0.034(4) -0.010(3) -0.011(3) -0.012(3) F5 0.042(5) 0.083(6) 0.040(4) -0.018(4) 0.003(4) -0.028(4) F6 0.047(5) 0.044(5) 0.045(4) -0.013(4) -0.014(4) -0.006(4) N1 0.032(6) 0.022(5) 0.027(5) -0.006(4) -0.006(4) -0.011(4) N2 0.032(6) 0.033(6) 0.025(5) 0.003(4) -0.008(4) -0.022(5) N3 0.030(5) 0.017(5) 0.030(5) -0.006(4) -0.010(4) -0.008(4) N4 0.040(6) 0.036(6) 0.020(5) -0.003(4) -0.008(4) -0.016(5) N5 0.032(6) 0.029(6) 0.047(6) -0.010(5) -0.015(5) -0.008(5) N6 0.044(7) 0.039(7) 0.037(6) -0.002(5) -0.016(5) -0.018(5) C1 0.040(7) 0.026(7) 0.030(6) 0.002(5) -0.009(6) -0.014(6) C2 0.048(8) 0.044(8) 0.022(6) 0.007(5) -0.009(6) -0.030(7) C3 0.018(6) 0.034(7) 0.032(6) -0.007(5) -0.003(5) -0.003(5) C4 0.038(7) 0.039(7) 0.017(5) -0.010(5) -0.001(5) -0.013(6) C5 0.039(7) 0.027(7) 0.026(6) -0.003(5) -0.004(5) -0.016(6) C6 0.033(7) 0.022(6) 0.024(6) -0.007(5) -0.005(5) -0.009(5) C7 0.046(8) 0.033(7) 0.026(6) -0.005(5) -0.015(6) -0.010(6) C8 0.045(8) 0.034(7) 0.019(5) 0.001(5) -0.017(5) -0.012(6) C9 0.047(8) 0.028(7) 0.037(7) -0.009(6) -0.009(6) -0.008(6) C10 0.024(6) 0.025(6) 0.025(6) -0.011(5) 0.002(5) -0.001(5) C11 0.042(8) 0.043(8) 0.046(8) -0.005(6) -0.005(7) -0.027(7) C12 0.034(8) 0.063(10) 0.067(10) -0.020(8) -0.017(7) -0.021(7) C13 0.053(9) 0.054(9) 0.037(7) -0.010(7) -0.023(7) -0.014(7) C14 0.036(8) 0.047(9) 0.026(6) 0.000(6) -0.009(6) -0.001(6) C15 0.038(8) 0.042(8) 0.051(8) 0.011(6) -0.029(7) -0.019(6) C16 0.052(9) 0.023(7) 0.044(8) 0.000(6) -0.009(7) -0.008(6) C17 0.043(8) 0.030(7) 0.035(7) 0.002(5) -0.014(6) -0.023(6) C18 0.056(9) 0.027(7) 0.046(8) 0.008(6) -0.027(7) -0.021(7) C19 0.050(9) 0.036(8) 0.065(10) 0.006(7) -0.024(8) -0.020(7) C20 0.032(7) 0.039(8) 0.042(8) 0.009(6) -0.007(6) -0.009(6) C21 0.025(7) 0.045(8) 0.039(7) 0.004(6) -0.012(6) -0.013(6) C22 0.038(7) 0.054(9) 0.031(6) 0.001(6) -0.009(6) -0.028(7) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' B B 0.0090 0.0039 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' I I -0.3257 6.8362 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag I3 I2 I1 177.20(4) . . ? F2 B1 F1 110.4(10) . . ? F2 B1 F3 109.2(11) . . ? F1 B1 F3 105.7(11) . . ? F2 B1 C15 111.1(12) . . ? F1 B1 C15 112.9(12) . . ? F3 B1 C15 107.3(10) . . ? F5 B2 F6 111.0(12) . . ? F5 B2 F4 107.6(12) . . ? F6 B2 F4 106.8(12) . . ? F5 B2 C22 110.3(13) . . ? F6 B2 C22 113.6(12) . . ? F4 B2 C22 107.2(11) . . ? C1 N1 C9 110.6(9) . . ? C1 N1 C8 110.1(9) . . ? C9 N1 C8 108.3(9) . . ? C3 N2 C15 111.7(9) . . ? C3 N2 C2 111.7(9) . . ? C15 N2 C2 113.1(9) . . ? C3 N2 H2 113(7) . . ? C15 N2 H2 106(6) . . ? C2 N2 H2 100(6) . . ? C5 N3 C4 110.2(9) . . ? C5 N3 C16 110.6(9) . . ? C4 N3 C16 108.7(9) . . ? C6 N4 C7 110.7(9) . . ? C6 N4 C22 114.8(10) . . ? C7 N4 C22 111.9(9) . . ? C6 N4 H4 107(8) . . ? C7 N4 H4 110(9) . . ? C22 N4 H4 103(9) . . ? C10 N5 C14 124.4(12) . . ? C10 N5 H5 127(9) . . ? C14 N5 H5 106(9) . . ? C21 N6 C17 122.4(12) . . ? C21 N6 H6 116(10) . . ? C17 N6 H6 121(10) . . ? N1 C1 C2 113.1(10) . . ? N1 C1 H1A 109.0 . . ? C2 C1 H1A 109.0 . . ? N1 C1 H1B 109.0 . . ? C2 C1 H1B 109.0 . . ? H1A C1 H1B 107.8 . . ? C1 C2 N2 111.2(9) . . ? C1 C2 H2A 109.4 . . ? N2 C2 H2A 109.4 . . ? C1 C2 H2B 109.4 . . ? N2 C2 H2B 109.4 . . ? H2A C2 H2B 108.0 . . ? C4 C3 N2 110.7(9) . . ? C4 C3 H3A 109.5 . . ? N2 C3 H3A 109.5 . . ? C4 C3 H3B 109.5 . . ? N2 C3 H3B 109.5 . . ? H3A C3 H3B 108.1 . . ? N3 C4 C3 113.4(9) . . ? N3 C4 H4A 108.9 . . ? C3 C4 H4A 108.9 . . ? N3 C4 H4B 108.9 . . ? C3 C4 H4B 108.9 . . ? H4A C4 H4B 107.7 . . ? N3 C5 C6 112.5(10) . . ? N3 C5 H5A 109.1 . . ? C6 C5 H5A 109.1 . . ? N3 C5 H5B 109.1 . . ? C6 C5 H5B 109.1 . . ? H5A C5 H5B 107.8 . . ? N4 C6 C5 110.8(9) . . ? N4 C6 H6A 109.5 . . ? C5 C6 H6A 109.5 . . ? N4 C6 H6B 109.5 . . ? C5 C6 H6B 109.5 . . ? H6A C6 H6B 108.1 . . ? C8 C7 N4 112.8(10) . . ? C8 C7 H7A 109.0 . . ? N4 C7 H7A 109.0 . . ? C8 C7 H7B 109.0 . . ? N4 C7 H7B 109.0 . . ? H7A C7 H7B 107.8 . . ? C7 C8 N1 112.7(9) . . ? C7 C8 H8A 109.0 . . ? N1 C8 H8A 109.0 . . ? C7 C8 H8B 109.0 . . ? N1 C8 H8B 109.0 . . ? H8A C8 H8B 107.8 . . ? N1 C9 C10 113.8(9) . . ? N1 C9 H9A 108.8 . . ? C10 C9 H9A 108.8 . . ? N1 C9 H9B 108.8 . . ? C10 C9 H9B 108.8 . . ? H9A C9 H9B 107.7 . . ? N5 C10 C11 118.1(11) . . ? N5 C10 C9 118.1(12) . . ? C11 C10 C9 123.7(12) . . ? C12 C11 C10 117.6(13) . . ? C12 C11 H11 121.2 . . ? C10 C11 H11 121.2 . . ? C13 C12 C11 121.5(13) . . ? C13 C12 H12 119.3 . . ? C11 C12 H12 119.3 . . ? C14 C13 C12 118.8(12) . . ? C14 C13 H13 120.6 . . ? C12 C13 H13 120.6 . . ? N5 C14 C13 119.5(14) . . ? N5 C14 H14 120.3 . . ? C13 C14 H14 120.3 . . ? N2 C15 B1 111.1(10) . . ? N2 C15 H15A 109.4 . . ? B1 C15 H15A 109.4 . . ? N2 C15 H15B 109.4 . . ? B1 C15 H15B 109.4 . . ? H15A C15 H15B 108.0 . . ? N3 C16 C17 112.3(10) . . ? N3 C16 H16A 109.1 . . ? C17 C16 H16A 109.1 . . ? N3 C16 H16B 109.1 . . ? C17 C16 H16B 109.1 . . ? H16A C16 H16B 107.9 . . ? C18 C17 N6 119.4(12) . . ? C18 C17 C16 123.9(12) . . ? N6 C17 C16 116.4(11) . . ? C17 C18 C19 120.6(13) . . ? C17 C18 H18 119.7 . . ? C19 C18 H18 119.7 . . ? C18 C19 C20 118.7(13) . . ? C18 C19 H19 120.7 . . ? C20 C19 H19 120.7 . . ? C21 C20 C19 117.7(13) . . ? C21 C20 H20 121.1 . . ? C19 C20 H20 121.1 . . ? N6 C21 C20 121.2(13) . . ? N6 C21 H21 119.4 . . ? C20 C21 H21 119.4 . . ? N4 C22 B2 111.8(10) . . ? N4 C22 H22A 109.3 . . ? B2 C22 H22A 109.3 . . ? N4 C22 H22B 109.3 . . ? B2 C22 H22B 109.3 . . ? H22A C22 H22B 107.9 . . ? loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag I1 I2 3.1287(12) . ? I2 I3 2.8235(13) . ? I4 I5 2.7901(14) . ? B1 F2 1.386(16) . ? B1 F1 1.409(16) . ? B1 F3 1.446(16) . ? B1 C15 1.619(19) . ? B2 F5 1.373(18) . ? B2 F6 1.394(19) . ? B2 F4 1.443(16) . ? B2 C22 1.594(19) . ? N1 C1 1.466(15) . ? N1 C9 1.478(14) . ? N1 C8 1.501(13) . ? N2 C3 1.508(14) . ? N2 C15 1.511(14) . ? N2 C2 1.521(14) . ? N2 H2 1.06(12) . ? N3 C5 1.481(14) . ? N3 C4 1.486(14) . ? N3 C16 1.493(14) . ? N4 C6 1.492(13) . ? N4 C7 1.505(15) . ? N4 C22 1.517(15) . ? N4 H4 0.90(12) . ? N5 C10 1.323(16) . ? N5 C14 1.343(16) . ? N5 H5 0.91(14) . ? N6 C21 1.321(16) . ? N6 C17 1.361(15) . ? N6 H6 0.852(10) . ? C1 C2 1.502(16) . ? C1 H1A 0.9900 . ? C1 H1B 0.9900 . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C3 C4 1.498(16) . ? C3 H3A 0.9900 . ? C3 H3B 0.9900 . ? C4 H4A 0.9900 . ? C4 H4B 0.9900 . ? C5 C6 1.526(15) . ? C5 H5A 0.9900 . ? C5 H5B 0.9900 . ? C6 H6A 0.9900 . ? C6 H6B 0.9900 . ? C7 C8 1.501(17) . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? C8 H8A 0.9900 . ? C8 H8B 0.9900 . ? C9 C10 1.492(16) . ? C9 H9A 0.9900 . ? C9 H9B 0.9900 . ? C10 C11 1.411(17) . ? C11 C12 1.385(18) . ? C11 H11 0.9500 . ? C12 C13 1.37(2) . ? C12 H12 0.9500 . ? C13 C14 1.354(19) . ? C13 H13 0.9500 . ? C14 H14 0.9500 . ? C15 H15A 0.9900 . ? C15 H15B 0.9900 . ? C16 C17 1.512(17) . ? C16 H16A 0.9900 . ? C16 H16B 0.9900 . ? C17 C18 1.355(17) . ? C18 C19 1.385(19) . ? C18 H18 0.9500 . ? C19 C20 1.432(19) . ? C19 H19 0.9500 . ? C20 C21 1.375(18) . ? C20 H20 0.9500 . ? C21 H21 0.9500 . ? C22 H22A 0.9900 . ? C22 H22B 0.9900 . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A _geom_hbond_publ_flag N2 H2 N1 1.06(12) 2.33(11) 2.942(13) 115(8) . yes N4 H4 F4 0.90(12) 2.23(13) 2.766(11) 118(10) . yes N4 H4 N3 0.90(12) 2.47(12) 2.943(13) 113(10) . yes N5 H5 F4 0.91(14) 1.89(14) 2.770(13) 162(13) . yes N6 H6 F3 0.852(10) 1.91(2) 2.759(13) 174(14) . yes C2 H2A I3 0.99 3.29 4.104(13) 140.8 2_666 yes C3 H3A I1 0.99 3.16 4.077(12) 154.1 1_655 yes C3 H3B F1 0.99 2.41 3.180(14) 134.3 . yes C4 H4A I6 0.99 3.28 4.259(12) 170.3 . yes C6 H6A I6 0.99 2.98 3.933(11) 161.6 . yes C6 H6B I2 0.99 3.19 3.964(12) 135.9 2_566 yes C7 H7B F6 0.99 2.34 3.130(14) 136.3 . yes C8 H8B I6 0.99 3.12 4.066(11) 161.2 . yes C9 H9A F6 0.99 2.63 3.526(17) 150.6 . yes C9 H9B I1 0.99 3.07 4.025(13) 163.6 2_576 yes C11 H11 I6 0.95 3.12 3.867(13) 136.6 2_676 yes C13 H13 I6 0.95 3.32 4.228(13) 161.8 1_556 yes C14 H14 I5 0.95 3.15 3.928(13) 140.7 1_556 yes C16 H16A F1 0.99 2.57 3.484(17) 153.0 . yes C16 H16B I6 0.99 3.02 3.982(13) 164.1 2_666 yes C18 H18 I1 0.95 3.18 3.897(13) 133.8 2_566 yes C20 H20 I2 0.95 3.18 3.959(13) 140.9 1_556 yes C21 H21 I4 0.95 3.20 4.053(13) 150.9 1_556 yes C22 H22B I3 0.99 3.27 4.146(12) 148.0 2_566 yes